Methanol → 2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde oxime

HRID 80145

Reaktionsgleichung

Reaktionsgleichung von HRID 80145
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][N:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[CH3:21])[C:11]2=[O:22])=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:24][OH:25].N1C=CC=CC=1.CO>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][N:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[CH3:21])[C:11]2=[O:22])=[CH:6][C:3]=1[CH:4]=[N:24][OH:25]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 866493982-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde

Produkt 1

HCID 866493992-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde oximeAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde (I-113a: 230 mg, 0.769 mmol), hydroxylamine hydrochloride (160 mg, 2.307 mmol) and pyridine (5 mL) were taken in a reaction flask and the flask was stirred at room temperature for 18 hours under nitrogen atmosphere. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ice water and ethylacetate. The organic layer was dried over Na2SO4 and concentrated. The concentrate was washed with diethyl ether and decanted to afford 170 mg of 2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde oxime (70.8% yield).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ice water and ethylacetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. washThe concentrate was washed with diethyl ether
  5. customdecanted

Quellen und Nachweise

ORD-Eintrag
ord-7ddcb20f0a0c4a60a4c0581e08054877
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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